Synthesis of asymmetrically substituted scyllo-inositol

被引：8
|
作者：
Rodriguez, Jacob [1 ]
Walczak, Maciej A. [1 ]
机构：
[1] Univ Colorado, Dept Chem & Biochem, Campus Box 215, Boulder, CO 80309 USA
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 30期
关键词：
scyllo-Inositol; Ferrier rearrangement; Inositols; STEREOSELECTIVE-SYNTHESIS; POSSIBLE REGIOISOMERS; MYOINOSITOL; TELOMERASE; 1,4,5-TRISPHOSPHATE; REARRANGEMENT; AGGREGATION; DERIVATIVES; PHOSPHATE; DISEASE;
D O I：
10.1016/j.tetlet.2016.06.038
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
scyllo-Inositol, a rare member of the inositol family, is present in axinelloside A, a marine metabolite with interesting inhibitory activity against human telomerase. Here, we present a concise synthesis of asymmetrically substituted scyllo-inositol starting from inexpensive n-glucose. Our synthetic approach capitalizes on Ferrier rearrangement of vinyl acetate and stereoselective reduction of the resultant ketone to establish the scyllo-inositol core. The protocol provides access to large quantities of scyllo-inositol in 10 steps from commercially available materials. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3281 / 3283
页数：3
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